Synthesis of orthogonally protected azalanthionines (lanazanines) by sequential ring-opening of N-substituted aziridine 2-carboxylates

Keith O'Brien; Keith Ó Proinsias; Fintan Kelleher

doi:10.1016/j.tetlet.2013.02.096

Synthesis of orthogonally protected azalanthionines (lanazanines) by sequential ring-opening of N-substituted aziridine 2-carboxylates

Keith O'Brien, Keith Ó Proinsias, Fintan Kelleher

School of Chemical and BioPharmaceutical Science

Research output: Contribution to journal › Article › peer-review

Abstract

Orthogonally protected azalanthionines (lanazanines, 4-azadiaminopimelic acids or β-aminoalaninoalanines) have been synthesised in good yields by the ring-opening of N-protected aziridine 2-carboxylates with suitably protected diaminopropanoic acids (DAPs). The required DAPs were also synthesised by ring-opening of N-protected aziridine 2-carboxylates with para- methoxybenzylamine.

Original language	English
Pages (from-to)	2395-2397
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2013.02.096
Publication status	Published - 8 May 2013

Keywords

Azalanthionine
Aziridine
Lanthionine
Ring-opening

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10.1016/j.tetlet.2013.02.096

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title = "Synthesis of orthogonally protected azalanthionines (lanazanines) by sequential ring-opening of N-substituted aziridine 2-carboxylates",

abstract = "Orthogonally protected azalanthionines (lanazanines, 4-azadiaminopimelic acids or β-aminoalaninoalanines) have been synthesised in good yields by the ring-opening of N-protected aziridine 2-carboxylates with suitably protected diaminopropanoic acids (DAPs). The required DAPs were also synthesised by ring-opening of N-protected aziridine 2-carboxylates with para- methoxybenzylamine.",

keywords = "Azalanthionine, Aziridine, Lanthionine, Ring-opening",

author = "Keith O'Brien and {{\'O} Proinsias}, Keith and Fintan Kelleher",

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doi = "10.1016/j.tetlet.2013.02.096",

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T1 - Synthesis of orthogonally protected azalanthionines (lanazanines) by sequential ring-opening of N-substituted aziridine 2-carboxylates

AU - O'Brien, Keith

AU - Ó Proinsias, Keith

AU - Kelleher, Fintan

PY - 2013/5/8

Y1 - 2013/5/8

N2 - Orthogonally protected azalanthionines (lanazanines, 4-azadiaminopimelic acids or β-aminoalaninoalanines) have been synthesised in good yields by the ring-opening of N-protected aziridine 2-carboxylates with suitably protected diaminopropanoic acids (DAPs). The required DAPs were also synthesised by ring-opening of N-protected aziridine 2-carboxylates with para- methoxybenzylamine.

AB - Orthogonally protected azalanthionines (lanazanines, 4-azadiaminopimelic acids or β-aminoalaninoalanines) have been synthesised in good yields by the ring-opening of N-protected aziridine 2-carboxylates with suitably protected diaminopropanoic acids (DAPs). The required DAPs were also synthesised by ring-opening of N-protected aziridine 2-carboxylates with para- methoxybenzylamine.

KW - Azalanthionine

KW - Aziridine

KW - Lanthionine

KW - Ring-opening

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

Synthesis of orthogonally protected azalanthionines (lanazanines) by sequential ring-opening of N-substituted aziridine 2-carboxylates

Abstract

Keywords

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